Cheap Flights from Milan to Chicago, IL from $318

Return flight: Chicago – Milan

On Cheapflightsplus.com you will find 2 direct and 999 connecting flights from Milan to Chicago. You can compare airfare deals from 46 airlines and multiple travel sites from $318, book and save on cheap plane tickets and last minute offers. Also check out MIL-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Flight Information

Below we will explain in detail what the flights cost on the destination from Milan to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Milan and Chicago is 7289 miles. Time difference between the cities is 7h. Airplanes depart 00:50 to 23:59 from 4 Milan airports and arrive 00:50 to 23:59 to 7 Chicago airports. Average flight time is 9h 50m.

  • The fastest flight 9h 50m
  • Average flight time 9h 50m
  • The earliest flight 00:50
  • The latest flight 23:59
  • Distance 4530 ml

The cheapest months to travel to Chicago are august (from 318 $), october (from 359 $), september (from 421 $).

The most expensive months are january (from 629 $), december (from 574 $), november (from 565 $).

What is the lowest airfare Milan to Chicago?

The cheapest plane ticket found by our users is $318. This airfare is for economy class on one-way FR2878 flight by Ryanair for August 27, 2025 which leaves Milan Bergamo (Orio al Serio) in Milan at 17:55 am and arrives at Chicago O'Hare International at 17:50.

Economy class
$318
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Business class
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First class
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Flight Schedule Milan to Chicago (Illinois)

10:35 — 19:17+1day
39h 42m flight time
Find flight
from$359
10:35 — 12:15 Milan — Barcelona
W46315 Aero Services Executive
6h 15m stop
18:30 — 21:40 Barcelona — New York
IB2627 Iberia
19h 55m stop
17:35 — 19:17 New York — Chicago
NK918 Spirit Airlines
11:20 — 17:50+1day
37h 30m flight time
Find flight
from$342
11:20 — 14:00 Milan — Oslo
U21989 EasyJet
6h 30m stop
20:30 — 22:55 Oslo — Helsinki
AY918 Finnair
17h 30m stop
16:25 — 17:50 Helsinki — Chicago
AY9 Finnair
13:00 — 17:50+1day
35h 50m flight time
Find flight
from$341
13:00 — 15:40 Milan — Hagersten
SK690 SAS
5h 40m stop
21:20 — 23:20 Hagersten — Helsinki
AY820 Finnair
17h 5m stop
16:25 — 17:50 Helsinki — Chicago
AY9 Finnair
13:00 — 17:50+1day
35h 50m flight time
Find flight
from$342
13:00 — 15:40 Milan — Hagersten
SK690 SAS
21h 35m stop
13:15 — 15:15 Hagersten — Helsinki
AY808 Finnair
1h 10m stop
16:25 — 17:50 Helsinki — Chicago
AY9 Finnair
14:00 — 17:50+1day
34h 50m flight time
Find flight
from$356
20:00 — 22:40 Milan — Oslo
DY1879 Norwegian
3h 50m stop
20:45 — 23:10 Oslo — Helsinki
AY918 Finnair
17h 30m stop
16:25 — 17:50 Helsinki — Chicago
AY9 Finnair
15:20 — 18:10
9h 50m flight time
Find flight
from$884
Milan — Chicago
UA415 United Airlines
15:20 — 18:10
9h 50m flight time
Find flight
from$1448
Milan — Chicago
LH7812 Lufthansa
17:55 — 17:50+1day
30h 55m flight time
Find flight
from$318
17:55 — 20:35 Milan — Hagersten
FR2878 Ryanair
11h 30m stop
08:05 — 10:05 Hagersten — Helsinki
AY802 Finnair
6h 20m stop
16:25 — 17:50 Helsinki — Chicago
AY9 Finnair
17:55 — 17:50+1day
30h 55m flight time
Find flight
from$318
17:55 — 20:35 Milan — Hagersten
FR2878 Ryanair
9h 45m stop
06:20 — 08:40 Hagersten — Helsinki
AY826 Finnair
7h 45m stop
16:25 — 17:50 Helsinki — Chicago
AY9 Finnair
17:55 — 17:50+1day
30h 55m flight time
Find flight
from$318
17:55 — 20:35 Milan — Hagersten
FR2878 Ryanair
16h 40m stop
13:15 — 15:15 Hagersten — Helsinki
AY808 Finnair
1h 10m stop
16:25 — 17:50 Helsinki — Chicago
AY9 Finnair
17:55 — 17:50+1day
30h 55m flight time
Find flight
from$318
17:55 — 20:35 Milan — Hagersten
FR2878 Ryanair
10h 40m stop
07:15 — 09:15 Hagersten — Helsinki
AY806 Finnair
7h 10m stop
16:25 — 17:50 Helsinki — Chicago
AY9 Finnair
17:55 — 17:50+1day
30h 55m flight time
Find flight
from$318
17:55 — 20:35 Milan — Hagersten
FR2878 Ryanair
16h 10m stop
12:45 — 14:45 Hagersten — Helsinki
AY804 Finnair
1h 40m stop
16:25 — 17:50 Helsinki — Chicago
AY9 Finnair
19:35 — 19:00+1day
30h 25m flight time
Find flight
from$359
19:35 — 22:15 Milan — Malaga
W46307 Aero Services Executive
14h 25m stop
12:40 — 14:45 Malaga — Dublin
EI581 Aer Lingus
1h 55m stop
16:40 — 19:00 Dublin — Chicago
EI125 Aer Lingus
20:45 — 17:50+1day
28h 5m flight time
Find flight
from$358
20:45 — 23:25 Milan — Hagersten
SK2690 SAS
13h 50m stop
13:15 — 15:15 Hagersten — Helsinki
AY808 Finnair
1h 10m stop
16:25 — 17:50 Helsinki — Chicago
AY9 Finnair
20:45 — 17:50+1day
28h 5m flight time
Find flight
from$358
20:45 — 23:25 Milan — Hagersten
SK2690 SAS
7h 50m stop
07:15 — 09:15 Hagersten — Helsinki
AY806 Finnair
7h 10m stop
16:25 — 17:50 Helsinki — Chicago
AY9 Finnair
Full flight schedule will help you in detecting at what time planes fly from Milan to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
*Departure and arrival times - local. Updated on October 13, 2025.

Popular Airlines on the Route

The flight Milan — Chicago is served by 46 regular airlines and 6 low-cost airlines. Most of the flights on this route are operated by Neos - 12 departures per week at the price of from $ 499 . And the most expensive tickets are offered by Lufthansa airline - from $ 1448.

Direct flights

There are 2 nonstop flights on the route. The fastest direct flight is UA415 by United Airlines takes 9h 50m and the cheapest is FR2878 by Ryanair for $884.

  • UA - United Airlines
    from $884
    Find
  • LH - Lufthansa
    from $1448
    Find
See more direct flights

Connecting Flights

There are 999 flights with layovers on the route. The fastest connecting flight is FR1455 by Ryanair takes 12h 15m and the cheapest is FR2878 by Ryanair for $318.

  • NO - Neos
    from $499
    Find
  • S4 - SATA International
    from $568
    Find
  • DE - Condor Airlines
    from $663
    Find
  • XZ - Ivoire Aero-Services
    from $433
    Find
  • VY - Vueling
    from $361
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  • FI - Icelandair
    from $456
    Find
  • LO - LOT
    from $525
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  • JU - Air Serbia
    from $483
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  • FR - Ryanair
    from $318
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  • LX - SWISS International Air Lines
    from $462
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  • A3 - Aegean Airlines
    from $727
    Find
  • BT - airBaltic
    from $776
    Find
See more connecting flights

Airports

You can fly from Milan to Chicago from 4 airports (Linate, Malpensa, Milan Bergamo (Orio al Serio), Segrate).

Milan airports

  • Linate-LIN
    from $341
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  • Malpensa-MXP
    from $356
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  • Milan Bergamo (Orio al Serio)-BGY
    from $318
    Find
  • Segrate-SWK
    Find

Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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